2-Decarboxy-2-hydroxymethyl-19-keto-PG compounds

ABSTRACT

The present invention provides novel 2-decarboxy-2-hydroxymethyl-19-keto-PG compounds, which are useful for a variety of pharmacological purposes, e.g., antiasthmatic indications.

DESCRIPTION CROSS REFERENCE TO RELATED APPLICATION

This application is a division of Ser. No. 025,879, filed Apr. 2, 1979, now pending.

BACKGROUND OF THE INVENTION

The present invention relates to novel prostaglandin analogs. Particularly, the invention relates to prostaglandin analogs wherein the C-19 position is substituted by oxo, i.e., 19-keto-PG compounds or 19-oxo-PG compounds. Most particularly, the present invention relates to novel 2-decarboxy-2-hydroxymethyl-19-keto-PGF compounds, a disclosure of the preparation and pharmacological use of which is incorporated here by reference from U.S. Ser. No. 025,899, filed Apr. 2, 1979, now U.S. Pat. No. 4,228,104 issued Oct. 14, 1980.

PRIOR ART

Prostaglandins exhibiting a variety of substitution at the C-19 position are known. See particularly J. C. Sih, et al., JACS 91:3685 (1969) wherein 19-oxo-PGE₂ and 13,14-dihydro-19-oxo-PGE₁ are disclosed. Further, Chemical Abstracts 86:43265H purportedly discloses 19-oxo-PGF₂ α. The abstract is derived from Japanese Kokai 76 82,245.

SUMMARY OF THE INVENTION

The present invention particularly provides: a compound of the formula ##STR1## wherein D is (1) cis-CH═CH-CH₂ -(CH₂)_(g) -CH₂ -,

(2) cis-CH═CH-CH₂ -(CH₂)_(g) -CF₂ -,

(3) cis-CH₂ -CH═CH-CH₂ -CH₂ -,

(4) trans-(CH₂)₃ -CH═CH-,

(5) -(CH₂)₃ -(CH₂)_(g) -CH₂ -,

(6) -(CH₂)₃ -CH₂ -CF₂ -,

(7) -(CH₂)₃ -O-CH₂ -,

(8) -(CH₂)-O-(CH₂)₂ -,

(9) -CH₂ -O-(CH₂)₃ -,

(10) -(m-Ph)-(CH₂)₂ -, or

(11) -(m-Ph)-O-CH₂ -,

wherein -(m-Ph)-is inter-meta-phenylene and

wherein g is zero, one, two, or three;

wherein Q is α-OH:β-R₅ or α-R₅ :β-OH, wherein R₅ is hydrogen or methyl;

wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl,

wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; and

wherein W is oxo, methylene, α-OH:β-H, or α-H:β-OH; and

wherein X is cis- or trans-CH═CH-, -C.tbd.C- or -CH₂ CH₂ -.

The compounds of the present invention are particularly useful for inducing prostaglandin-like biological effects, as described in U.S. Ser. No. 026,066. Uses of compounds in accordance with the present invention include, therefore, antiasthmatic indications.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The present invention particularly relates to:

2-decarboxy-2-hydroxymethyl-19-keto-PGF₂ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₂ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF.sub.1 α,

2-decarboxy-2-hydroxymethyl-19-keto-PGF₂ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₂ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF.sub.2 β,

2-decarboxy-2-hydroxymethyl-19-keto-PGE₂,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGE₂,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGE.sub.2,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-19-keto-PGE₂,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-19-keto-PGE₂,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxo-11α-hydroxymethyl-19-keto-PGE₂,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGF.sub.1 α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGF.sub.1 β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-16,16-difluoro-PGF₁ β,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGE₁

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ α,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ β,

2-decarboxy-2-hydroxymethyl-2.3-didehydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGE₁

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁,

2-decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁,

2-decarboxy-2-hydroxymethyl-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF.sub.1 α,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ α,

2-decarboxy-2-hydroxymethyl-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGF₂ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-ket-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF.sub.1 β,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ β,

2-decarboxy-2-hydroxymethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-16,16-difluoro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxyemthyl-19-keto-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-dimethyl-19-keto-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-difluoro-19-keto-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-13,14-dihydro-19-keto-PGE.sub.1,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-dimethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-13,14-dihydro-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁,

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGE₁, and

2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGE₁. 

I claim:
 1. A compound of the formula ##STR2## wherein D is (1) cis-CH═CH-CH₂ -(CH₂)_(g) -CH₂ -,(2) cis-CH═CH-CH₂ -(CH₂)_(g) -CF₂ -, (3) cis-CH₂ -CH═CH-CH₂ -CH₂ -, (4) trans-(CH₂)₃ -CH═CH-, (5) -(CH₂)₃ -(CH₂)_(g) -CH₂ -, (6) -(CH₂)₃ -CH₂ -CF₂ -, (7) -(CH₂)₃ -O-CH₂ -, (8) -(CH₂)-O-(CH₂)₂ -, (9) -CH₂ -O-(CH₂)₃ -, (10) -(m-Ph)-(CH₂)₂ -, or (11) -(m-Ph)-O-CH₂ -,wherein -(m-Ph)- is inter-meta-phenylene and wherein g is zero, one, two, or three; wherein Q is α-OH:β-R₅ or α-R₅ :β-OH, wherein R₅ is hydrogen or methyl; wherein R₂ is hydrogen, hydroxyl, or hydroxymethyl, wherein R₃ and R₄ are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R₃ and R₄ is fluoro only when the other is hydrogen or fluoro; and wherein W is oxo, methylene, α-OH:β-H, or α-H:β-OH; and wherein X is cis- or trans-CH═CH-, -C.tbd.C- or -CH₂ CH-.
 2. A compound according to claim 1, wherein D is cis-CH═CH-CH₂ -(CH₂)_(g) -CH₂ -.
 3. A compound according to claim 2, wherein W is α-OH:β-H.
 4. A compound according to claim 3, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 5. 2-Decarboxy-2-hydroxymethyl-19-keto-PGF₂ α, a compound according to claim
 4. 6. A compound according to claim 3, wherein R₂ is hydrogen and X is trans-CH═CH-.
 7. 2-Decarboxy-3-hydroxymethyl-11-deoxy-19-keto-PGF₂ α, a compound according to claim
 6. 8. A compound according to claim 3, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 9. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF₂ α, a compound according to claim
 8. 10. A compound according to claim 2, wherein W is α-OH:β-H.
 11. A compound according to claim 10, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 12. 2-Decarboxy-2-hydroxymethyl-19-keto-PGF₂ α, a compound according to claim
 11. 13. A compound according to claim 10, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 14. 2-Decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₂ β, a compound according to claim
 13. 15. A compound according to claim 10, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 16. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF₂ β, a compound according to claim
 15. 17. A compound according to claim 2, wherein W is oxo.
 18. A compound according to claim 17, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 19. 2-Decarboxy-2-hydroxymethyl-19-keto-PGE₂, a compound according to claim
 18. 20. A compound according to claim 17, wherein R₂ is hydrogen and X is trans-CH═CH-.
 21. 2-Decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGE₂, a compound according to claim
 20. 22. A compound according to claim 17, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 23. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGE₂, a compound according to claim
 22. 24. A compound according to claim 2, wherein W is methylene.
 25. A compound according to claim 24, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 26. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-19-keto-PGE₂, a compound according to claim
 25. 27. A compound according to claim 24, wherein R₂ is hydrogen and X is trans-CH═CH-.
 28. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-19-keto-PGE₂, a compound according to claim
 27. 29. A compound according to claim 24, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 30. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19-keto-PGE.sub.2, a compound according to claim
 29. 31. A compound according to claim 1, wherein D is cis-CH₂ -CH═CH-CH₂ -CH₂ -.
 32. A compound according to claim 31, wherein W is β-OH:α-H.
 33. A compound according to claim 32, wherein R₂ is hydroxyl.
 34. A compound according to claim 33, wherein X is trans-CH═CH-.
 35. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGF₁ α, a compound according to claim
 34. 36. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGF₁ α, a compound according to claim
 34. 37. A compound according to claim 33, wherein X is -C.tbd.C-.
 38. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGF₁ α, a compound according to claim
 37. 39. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGF₁ α, a compound according to claim
 37. 40. A compound according to claim 32, wherein R₂ is hydrogen.
 41. A compound according to claim 40, wherein X is trans-CH═CH-.
 42. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGF₁ α, a compound according to claim
 41. 43. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ α, a compound according to claim
 41. 44. A compound according to claim 32, wherein R₂ is hydroxymethyl.
 45. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGF₁ α, a compound according to claim
 44. 46. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ α, a compound according to claim
 44. 47. A compound according to claim 32, wherein R₂ is hydroxymethyl.
 48. A compound according to claim 47, wherein X is trans-CH═CH-.
 49. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGF₁ α, a compound according to claim
 48. 50. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ α, a compound according to claim
 48. 51. A compound according to claim 47, wherein X is -C.tbd.C-.
 52. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ α, a compound according to claim
 51. 53. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁ α, a compound according to claim
 51. 54. A compound according to claim 31, wherein W is β-OH:α-H.
 55. A compound according to claim 54, wherein R₂ is hydroxyl.
 56. A compound according to claim 55, wherein X is trans-CH═CH-.
 57. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGF₁ β, a compound according to claim
 56. 58. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGF₁ β, a compound according to claim
 56. 59. A compound according to claim 55, wherein X is -C.tbd.C-.
 60. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGF₁ β, a compound according to claim
 59. 61. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGF₁ β, a compound according to claim
 59. 62. A compound according to claim 54, wherein R₂ is hydrogen.
 63. A compound according to claim 62, wherein X is trans-CH═CH-.
 64. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGF₁ β, a compound according to claim
 63. 65. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ β, a compound according to claim
 63. 66. A compound according to claim 62, wherein X is -C.tbd.C-.
 67. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGF₁ β, a compound according to claim
 66. 68. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ β, a compound according to claim
 66. 69. A compound according to claim 54, wherein R₂ is hydroxymethyl.
 70. A compound according to claim 69, wherein X is trans-CH═CH-.
 71. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGF₁ β, a compound according to claim
 70. 72. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-15(S)-15-methyl-PGF₁ β, a compound according to claim
 70. 73. A compound according to claim 69, wherein X is -C.tbd.C-.
 74. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ β, a compound according to claim
 73. 75. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁ β, a compound according to claim
 73. 76. A compound according to claim 31, wherein W is oxo.
 77. A compound according to claim 76, wherein R₂ is hydroxyl.
 78. A compound according to claim 77, wherein X is trans-CH═CH-.
 79. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-PGE₁, a compound according to claim
 78. 80. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-15(S)-15-methyl-PGE₁, a compound according to claim
 78. 81. A compound according to claim 77, wherein X is -C.tbd.C-.
 82. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-PGE₁, a compound according to claim
 81. 83. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-16,16-difluoro-PGE₁, a compound according to claim
 81. 84. A compound according to claim 76, wherein R₂ is hydrogen.
 85. A compound according to claim 84, wherein X is trans-CH═CH-.
 86. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-PGE₁, a compound according to claim
 85. 87. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGE₁, a compound according to claim
 85. 88. A compound according to claim 84, wherein X is -C.tbd.C-.
 89. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-PGE₁, a compound according to claim
 88. 90. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-16,16-difluoro-PGE₁, a compound according to claim
 88. 91. A compound according to claim 76, wherein R₂ is hydroxymethyl.
 92. A compound according to claim 91, wherein X is trans-CH═CH-.
 93. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-PGE₁, a compound according to claim
 92. 94. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, a compound according to claim
 92. 95. A compound according to claim 91, wherein X is -C.tbd.C-.
 96. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGE₁, a compound according to claim
 95. 97.2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-11-deoxy-11.alpha.-hydroxymethyl-16,16-difluoro-PGE₁, a compound according to claim
 95. 98. A compound according to claim 31, wherein W is methylene.
 99. A compound according to claim 98, wherein R₂ is hydroxyl.
 100. A compound according to claim 99, wherein X is trans-CH═CH-.
 101. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-PGE₁, a compound according to claim
 100. 102. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁, a compound according to claim
 100. 103. A compound according to claim 99, wherein X is -C.tbd.C-.
 104. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-PGE₁, a compound according to claim
 103. 105. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-16,16-difluoro-PGE₁, a compound according to claim
 103. 106. A compound according to claim 98, wherein R₂ is hydrogen.
 107. A compound according to claim 106, wherein X is trans-CH═CH-.
 108. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁, a compound according to claim
 107. 109. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-15(S)-15-methyl-PGE₁, a compound according to claim
 107. 110. A compound according to claim 106, wherein X is -C.tbd.C-.
 111. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁, a compound according to claim
 110. 112. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁, a compound according to claim
 110. 113. A compound according to claim 98, wherein R₂ is hydroxymethyl.
 114. A compound according to claim 113, wherein X is trans-CH═CH-.
 115. 2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, a compound according to claim
 114. 116.2-Decarboxy-2-hydroxymethyl-4,5-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, a compound according to claim
 114. 117. A compound according to claim 113, wherein X is -C.tbd.C-.
 118. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, a compound according to claim
 117. 119. 2-Decarboxy-2-hydroxymethyl-4,5,13,14-tetradehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11.alpha.-hydroxymethyl-16,16-difluoro-PGE₁, a compound according to claim
 117. 120. A compound according to claim 1, wherein D is trans-(CH₂)₃ -CH═CH-.
 121. A compound according to claim 120, wherein W is α-OH:β-H.
 122. A compound according to claim 121, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 123. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-PGF₁ α, a compound according to claim
 122. 124. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGF₁ α, a compound according to claim
 122. 125. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGF₁ α, a compound according to claim
 122. 126. A compound according to claim 121, wherein R₂ is hydrogen and X is trans-CH═CH-.
 127. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGF₁ α, a compound according to claim
 126. 128. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ α, a compound according to claim
 126. 129. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ α, a compound according to claim
 126. 130. A compound according to claim 121, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 131. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ α, a compound according to claim
 130. 132. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁ α, a compound according to claim
 130. 133. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ α, a compound according to claim
 130. 134. A compound according to claim 120, wherein W is β-OH:α-H.
 135. A compound according to claim 134, wherein R₂ is hydroxyl and X is trans-CH═C-.
 136. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-PGF₁ β, a compound according to claim
 135. 137. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGF₁ β, a compound according to claim
 135. 138. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGF₁ β, a compound according to claim
 135. 139. A compound according to claim 134, wherein R₂ is hydrogen and X is trans-CH═CH-.
 140. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGF₁ β, a compound according to claim
 139. 141. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGF₁ β, a compound according to claim
 139. 142. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGF₁ β, a compound according to claim
 139. 143. A compound according to claim 134, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 144. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGF₁ β, a compound according to claim
 143. 145. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGF₁ β, a compound according to claim
 143. 146. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGF₁ β, a compound according to claim
 143. 147. A compound according to claim 120, wherein W is oxo.
 148. A compound according to claim 147, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 149. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-PGE₁, a compound according to claim
 148. 150. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-16,16-difluoro-PGE₁, a compound according to claim
 148. 151. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-15(S)-15-methyl-PGE₁, a compound according to claim
 148. 152. A compound according to claim 147, wherein R₂ is hydrogen and X is trans-CH═CH-.
 153. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-PGE₁, a compound according to claim
 152. 154. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-16,16-difluoro-PGE₁, a compound according to claim
 152. 155. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-15(S)-15-methyl-PGE₁, a compound according to claim
 152. 156. A compound according to claim 147, wherein R₂ is hydroxymethyland X is trans-CH═CH-.
 157. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-PGE₁, a compound according to claim
 156. 158. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE.sub.1, a compound according to claim
 156. 159. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, a compound according to claim
 156. 160. A compound according to claim 120, wherein W is methylene.
 161. A compound according to claim 160, wherein R₂ is hydroxyl and X is trans-CH═CH-.
 162. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-PGE₁, a compound according to claim
 161. 163. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-16,16-difluoro-PGE₁, a compound according to claim
 161. 164. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxy-9-methylene-15(S)-15-methyl-PGE₁, a compound according to claim
 161. 165. A compound according to claim 160, wherein R₂ is hydrogen and X is trans-CH═CH-.
 166. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-PGE₁, a compound according to claim
 165. 167. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-PGE₁, a compound according to claim
 165. 168. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-15(S)-15-methyl-PGE₁, a compound according to claim
 165. 169. A compound according to claim 160, wherein R₂ is hydroxymethyl and X is trans-CH═CH-.
 170. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-PGE₁, a compound according to claim
 169. 171. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-PGE₁, a compound according to claim
 169. 172. 2-Decarboxy-2-hydroxymethyl-2,3-didehydro-19-keto-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-15(S)-15-methyl-PGE₁, a compound according to claim
 169. 173. A compound according to claim 1, wherein D is -(CH₂)₃ -(CH₂)_(g) -CH₂ -.
 174. A compound according to claim 173, wherein g is one.
 175. A compound according to claim 174, wherein W is α-OH:β-H.
 176. A compound according to claim 175, wherein R₂ is hydroxyl.
 177. A compound according to claim 176, wherein X is trans-CH═CH-.
 178. 2-Decarboxy-2-hydroxymethyl-19-keto-PGF₁ α, a compound according to claim
 177. 179. 2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ α, a compound according to claim
 177. 180. 2-Decarboxy-2-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ α, a compound according to claim
 177. 181. A compound according to claim 176, wherein X is -CH₂ CH₂ -.
 182. 2-Decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ α, a compound according to claim
 181. 183. A compound according to claim 175, wherein R₂ is hydrogen.
 184. A compound according to claim 183, wherein X is trans-CH═CH-.
 185. 2-Decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₁ α, a compound according to claim
 184. 186. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGF₁ α, a compound according to claim
 184. 187. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGF₁ α, a compound according to claim
 184. 188. A compound according to claim 183, wherein X is -CH₂ CH₂ -.
 189. 2-Decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGF₁ α, a compound according to claim
 188. 190. A compound according to claim 175, wherein R₂ is hydroxymethyl.
 191. A compound according to claim 190, wherein X is trans-CH═CH-.
 192. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF₁ α, a compound according to claim
 191. 193. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ α, a compound according to claim
 191. 194. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ α, a compound according to claim
 191. 195. A compound according to claim 190, wherein X is -CH₂ CH₂ -.
 196. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ α, a compound according to claim
 195. 197. A compound according to claim 174, wherein W is β:OH:α-H.
 198. A compound according to claim 197, wherein R₂ is hydroxyl.
 199. A compound according to claim 198, wherein X is trans-CH═CH-.
 200. 2-Decarboxy-2-hydroxymethyl-19-keto-PGF₁ α, a compound according to claim
 199. 201. 2-Decarboxy-2-hydroxymethyl-19-keto-16,16-dimethyl-PGF₁ β, a compound according to claim
 199. 202. 2-Decarboxy-2-hydroxymethyl-19-keto-16,16-difluoro-PGF₁ β, a compound according to claim
 199. 203. A compound according to claim 198, wherein X is -CH₂ CH₂ -.
 204. 2-Decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGF₂ β, a compound according to claim
 203. 205. A compound according to claim 197, wherein R₂ is hydrogen.
 206. A compound according to claim 205, wherein X is trans-CH═CH-.
 207. 2-Decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGF₁ β, a compound according to claim
 206. 208. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGF₁ β, a compound according to claim
 206. 209. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGF₁ β, a compound according to claim
 206. 210. A compound according to claim 205, wherein X is -CH₂ CH₂ -.
 211. 2-Decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGF₁ β, a compound according to claim
 210. 212. A compound according to claim 197, wherein R₂ is hydroxymethyl.
 213. A compound according to claim 212, wherein X is trans-CH═CH-.
 214. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGF₁ β, a compound according to claim
 213. 215. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGF₁ β, a compound according to claim
 213. 216. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGF₁ β, a compound according to claim
 213. 217. A compound according to claim 212, wherein X is -CH₂ CH₂ -.
 218. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGF₁ β, a compound according to claim
 217. 219. A compound according to claim 174, wherein W is oxo.
 220. A compound according to claim 219, wherein R₂ is hydroxyl.
 221. A compound according to claim 220, wherein X is trans-CH═CH-.
 222. 2-Decarboxy-2-hydroxymethyl-19-keto-PGE₁, a compound according to claim
 221. 223. 2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 221. 224. 2-Decarboxy-2-hydroxymethyl-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 221. 225. A compound according to claim 220, wherein X is -CH₂ CH₂ -.
 226. 2-Decarboxy-2-hydroxymethyl-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 225. 227. A compound according to claim 219, wherein R₂ is hydrogen.
 228. A compound according to claim 227, wherein X is trans-CH═CH-.
 229. 2-Decarboxy-2-hydroxymethyl-11-deoxy-19-keto-PGE₁, a compound according to claim
 228. 230. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 228. 231. 2-Decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 228. 232. A compound according to claim 227, wherein X is -CH₂ CH₂ -.
 233. 2-Decarboxy-2-hydroxymethyl-11-deoxy-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 232. 234. A compound according to claim 219, wherein R₂ is hydroxymethyl.
 235. A compound according to claim 234, wherein X is trans-CH═CH-.
 236. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19-keto-PGE₁, a compound according to claim
 235. 237. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 235. 238. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 235. 239. A compound according to claim 234, wherein X is -CH₂ CH₂ -.
 240. 2-Decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 239. 241. A compound according to claim 174, wherein W is methylene.
 242. A compound according to claim 241, wherein R₂ is hydroxyl.
 243. A compound according to claim 242, wherein X is trans-CH═CH-.
 244. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-19-keto-PGE₁, a compound according to claim
 243. 245. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 243. 246. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 243. 247. A compound according to claim 242, wherein X is -CH₂ CH₂ -.
 248. 2-Decarboxy-2-hydroxymethyl-9-deoxy-9-methylene-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 247. 249. A compound according to claim 241, wherein R₂ is hydrogen.
 250. A compound according to claim 249, wherein X is trans-CH═CH-.
 251. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-19-keto-PGE.sub.1, a compound according to claim
 250. 252. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 250. 253. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 250. 254. A compound according to claim 249, wherein X is -CH₂ CH₂ -.
 255. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 254. 256. A compound according to claim 241, wherein R₂ is hydroxymethyl.
 257. A compound according to claim 256, wherein X is trans-CH═CH-.
 258. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19-keto-PGE₁, a compound according to claim
 257. 259. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19-keto-PGE₁, a compound according to claim
 257. 260. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19-keto-PGE₁, a compound according to claim
 257. 261. A compound according to claim 256, wherein X is -CH₂ CH₂ -.
 262. 2-Decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-13,14-dihydro-19-keto-PGE₁, a compound according to claim
 261. 